2023 year in review

Happy 2024! It's time for my annual review for 2023.

For the last ten years, I've been sharing my thoughts and reflections in a year-in-review post each year. As a collective, these reviews describe my entire bootstrapping journey, both the breakthroughs and the struggles.

(You can read 2022, 2021, 2020201920182017201620152014, and 2013 here).

The big life question

Every year, I ask myself: "What am I optimizing my life for?" My current answer is:

I'm optimizing for a good life.

A "good life" doesn't mean my life is perpetually easy, perfect, or always happy. For me, a good life means:

  • Maximizing my life for freedom, simplicity, creativity, fun, learning, enjoyment, and self-actualization.

  • Realizing my potential and contributing to the potential of other humans.

  • Pursuing meaningful activities with people that I love.

  • Building and sustaining healthy communities.

  • Earning enough money to live well.

  • Living ethically and with integrity.

  • Investing in relationships.

An important part of my journey was realizing that business is a means to an end. Running a business shouldn't make us miserable. Instead, it should serve the purpose of enhancing our lives. A healthy business has healthy margins and should enable you to have a better life.

Transistor update

Transistor is my main business. It's a podcast hosting and analytics platform I co-founded with Jon Buda in 2018.

The Transistor team has five full-time people: Josh, Jason, Helen, Jon, and myself. We also hired Michael part-time this past year to help with customer support (not pictured).

Overall feelings

January 2024 will mark six years of Jon and I working on Transistor together. That's wild because, in my head, it only feels like three years.

I love our team. I love our customers (podcasters). I love our product. This is the best job I've ever had. I feel an enormous amount of gratitude that I get to earn a living doing this work with these people.

On the other hand, six years is also a weird milestone for a founder. As an entrepreneur, so much of your journey is dedicated to building something that works. What happens once you achieve that goal?

For Jon and me, our initial goal was to be able to quit our other jobs and go full-time on Transistor. We achieved that in 2019:

In 2020, my goal was to rebuild my personal financial margin: I paid off my line of credit, rebuilt my savings, and regularly contributed to my retirement fund again.

In 2021, Jon and I started optimizing the company to make our lives easier. We hired Helen in April to be in charge of customer support and Jason in August to help Jon on the engineering side.

And since 2021, I think Jon and I have been searching for new goals to motivate us. Some people get motivated by growth, the thought of being acquired, or hiring hundreds of people. But that's not really us.

Over the past year, I've been thinking about two dimensions of our work that are meaningful for me:

  • The product exists to make our customers’ lives better.

  • The company exists to make our team members' lives better.

Our team gets excited about building a great experience for our customers. Unlike so many other jobs, we have a direct connection with our customers: we can see the effect of our work because customers tell us about it! It's gratifying to show up daily and get to do good work that has an impact.

Doing meaningful work is one way that Transistor has made our lives better. But the company has done so much more for me (and, I believe, for our team members).

These feelings were mirrored by Ben Gilbert's experience of transitioning to full-time work on the Acquired podcast:

This project has led to so many things that have made building a family possible. The house I'm standing in is thanks to Acquired. The lifestyle I enjoy is a hundred percent Acquired, the fact that I wander around all day listening to audiobooks, the thing that it's done to my demeanor and my personality. Truly, the life that myself and my family enjoy is because of what we've built.

I'm thankful for all this; I don't take it for granted. And, as much as possible, I'd like to ensure that it continues. But it feels like we don't have a big overarching goal as we used to when trying to reach profitability. Maybe that's OK? We built something that's working; maybe it's enough to ensure that it continues to work.

Less lonely, less stressed, more productive

Last year, I wrote that I was "feeling the need for collaboration." Much of this came from observing Jon and Jason working together on the engineering side. I longed for that kind of energy and collaboration on the marketing side of the business.

Hiring Josh Anderton

Enter Joshua Anderton. I started working with Josh as a part-time contractor in October 2022. After accomplishing a ton together on the marketing site, we decided to bring him on full-time on March 27, 2023.

This past year, Josh and I have shipped a ton of new features on the marketing site:

Josh also helped design an updated embeddable player and designed and launched a new website theme.

Hiring Michael Green

Since we launched in 2018, I've done much of Transistor's customer support. Customer service is hugely important to me; I think it's one of the most important "features" a SaaS has.

When we hired Helen, she covered all the time zones I couldn't and took over doing our demo calls. This was a huge relief, but I was still answering tickets constantly, from when I woke up until I went to bed every day (including weekends and holidays).

It meant I was never present at home, with my family, or with friends.

I met Michael at a local tech meetup here in Vernon. He was looking to transition his career into the tech industry. I asked him if he'd be willing to cover our customer support during the summer-fall months to give me a reprieve while traveling.

Because he was local, he could come to my office and have me train him there. Within a few weeks, he confidently responded to customer inquiries on our live chat. And since then, he's been absolutely killing it. We regularly get messages like this from customers:

Since Michael and I met earlier this year, we've become good friends. He's also the funniest person I met in 2023.

Three mini divisions

What's great is each of us now has a mini team of two:

  • Customer success: Helen and Michael

  • Marketing: Justin and Josh

  • Engineering: Jon and Jason

Team retreat

Last year was our first team retreat (in Montreal). For our 2023 retreat, we traveled to Nashville, Tennessee.

Getting together as a team (at least once a year) is incredibly important when you work remotely.

There's no substitute for playing games, eating meals, and making memories together. It's like reapplying a fresh layer of glue to the team: I leave that week feeling more connected and aligned.

Before the retreat, Jon and I revised our Company Handbook, which was immensely clarifying (for both of us and hopefully the team).

It describes how we work at Transistor: what we value, how decisions are made, and our vision for the future. The hope is that it will help the team feel like we're on the same page and have reasonable expectations of each other and our work.

One of our main objectives for the retreat was to have fun together (and make memories). A few memorable highlights were:

  • Going to the Grande Ole Opry together.

  • Sharing some incredible meals at excellent restaurants.

  • Cruising down Broadway and marvelling at all the incredible musicians there.

  • Playing card games together (specifically "Cheat") and Jackbox games on the Nintendo Switch.

  • Hiring a photographer, going on a "photo walk" of Nashville, and getting these hilarious shots of the team together.

New Transistor features launched in 2023

As a team, we love observing podcasters, getting customer insights, imagining solutions, and launching new features. Here's some of what we launched this past year:

How we think about building new features

Committing to build a feature is like making a bet. In our new Handbook, we explored the question "Why do we build new features?" and came up with these answers:

  • improve the experience of existing customers,

  • help us attract new customers or new revenue,

  • improve our experience as team members,

  • be fun/interesting for us to work on.

We also created a framework for evaluating potential new features from a company perspective:

  • Does this decision match up with our values?

  • Is this decision going to make working at Transistor more busy, more complicated, and less fun?

  • Will this decision increase our customer support load?

  • What’s our primary motivation for this? Is it customer-focused, or is it a reaction to something that doesn't matter?

One feature, our delegated delivery integration with Apple, was a particularly hard slog (especially for Jason and Jon). I had pushed for it because it makes a future feature (that could benefit new podcasters) possible. But I realized we can't push through too many of those "hard slog" features. They can be draining.


In addition to traveling to Nashville for the team retreat, I got to go on some great trips this year.

Podcast Movement

Jon and Josh joined me in Denver, Colorado, for Podcast Movement this year. This is "the" big event for the podcast industry in North America. It allows us to meet face-to-face with some of Transistor's bigger partners (Apple Podcasts and Spotify) and interact with customers and other podcasting friends.


I was invited to speak at Full Stack Europe this year, so my wife and I decided to go together. In addition to the conference, we explored Amsterdam, Antwerp, and Berlin and met some amazing people.

The whole experience was incredible. Somebody said: "Time slows down when traveling because you're experiencing so many new things. You're out of your comfort zone the whole time."

Our train trip to Berlin was particularly fun for me. I'm a big fan of trains, but living in the Pacific Northwest of North America, we don't have good passenger rail. I loved traveling from Antwerp's (beautiful!) train station to Berlin, enjoying the view, going to the restaurant car, and working on the train.

A new experiment: The Family Business™

Even before I started Transistor with Jon, I had my own corporation (Nerd North Inc.).

Under that banner, I did consulting, launched products, operated a coworking office, organized local events, and launched side projects.

I like the flexibility of maintaining my own company (aside from Transistor). It's allowed me to invest in new experiments and try new projects independently. It's like my personal idea lab.

My wife and I have always run the business together, but I wanted to figure out how to get my kids involved.

Over the summer, we decided to hire all four (aged 14-21).

I assign them three types of projects:

  1. Creative work for the business: video editing, thumbnail creation, animation, copyediting.

  2. Creative projects they were interested in exploring: making a video game, animation projects, coding projects.

  3. Admin work: bookkeeping, software upgrades, server maintenance, answering email, running payroll.

There are four big motivations for hiring my kids:

  1. Spend more time with them: my daughter is going to college in a different city, and we don't get to see each other much. But now, every week, we have a call where she helps me do all the administrative tasks I've been procrastinating on. In the second half of the call, she reviewed other indie creators' newsletters for me and gave me tips on what I could incorporate. Likewise, I've been able to spend a lot more time with my three boys (who all live at home) because we almost always have a project to discuss.

  2. Teach them what I know about tech and business: making money takes practice, and I want to give them opportunities to build and launch their projects and earn an income from them. We're especially focused on what it takes to ship a project. (It's one thing to experiment, but quite another to get it out the door).

  3. Run more experiments: we have the margin to try things. I want to return to making more things (similar to when I made 100 things in a year). Doing it with my kids will be a lot of fun.

  4. Get more done: running a business takes a lot of work. All four of my kids are old enough to help me with tasks (video editing, bookkeeping, cleaning, etc), learn new skills, and have a real impact on our business. They get to be part of how our family earns an income.

Overall, this was one of my favorite things I did in 2023. It hasn't been perfect, but I can see the potential for us to try a lot of new projects together in 2024.

Here are a few ideas we're thinking about exploring:

  • Launching an indie video game on Steam (and attending a few indie game events).

  • Launching a new YouTube channel and blog reviewing tech, cars, and outdoor equipment.

  • Launching a mini-SaaS/web application together.

What else happened in 2023?

I spent many great days snowboarding at Silverstar Mountain and Revelstoke with family and friends.

I bought a Loopstation (RC505 Mark II) and enjoyed making audio loops (I published some of them on TikTok, much to my kids' chagrin).

I saw lots of live music: Exodus, Anthrax, Herbie Hancock, and many local bands. My wife and I also went to the Rifflandia festival with our daughter Sadie, which was really fun.

Plus, I saw Iron Maiden (one of my favorite bands) TWICE, in Edmonton and Vancouver. I brought my three teenage boys and met up with my brother and friends at both shows.

My wife helped me turn my office into an awesome YouTube/podcasting studio. She took Kevin Shen's Dreamstudio course, which was hugely helpful. She bought all the lights, the camera, the lenses, and sourced dozens of retro radios (tube and transistor!) for the backdrop.

I really like how it turned out!

Other highlights:

  • I hosted Geek Beers meetups and a handful of Hack Nights here in Vernon

  • Our daughter Sadie (attending school in Victoria) visited us over the Christmas holiday.

  • My eldest son, Marty, graduated from high school! (He also got his license and bought his first car).

  • My wife and I spent much time on the water, paddleboarding.

  • We had an awesome camping trip with friends close to Revelstoke in the summer.

  • My sister, her husband, my nieces, and my nephew all came to visit in August.

  • Walking to work with my friend Andy most days of the week.

  • Working alongside incredible people at Cowork Vernon, especially my friend Marco (who helps run it with me).

  • Saturday morning "coffee klatches" at Ratio with Mahlon, Daryl, Yuri, and whoever else showed up.

  • We spent many days at the beach.

  • I did a road trip to Silverwood Theme Park with my two youngest boys in August.

  • MegaMaker (the private community for bootstrappers I started) celebrated 10 years!

  • I saw many amazing sunsets.

  • I went to one yoga class.

  • I started working out in the mornings.

Not awesome:

  • I had a downhill mountain biking accident and split my arm open.

  • Wildfire decimated nearby Kelowna and caused a summer filled with bad smoke and air quality.

Ideas, goals, and plans for 2024

  • Planning on going to Podcast Movement in Washington, August 19-22.

  • I want to do a snowboarding trip in Revelstoke with my brother.

  • I want to start investing in (and advising) other indie SaaS businesses. I'm especially interested in founders coming out of the Laravel community.

  • I want to plan a trip for the family during my boys' spring break.

  • I want to plan a trip in August for the whole family (it will likely need to be somewhere not affected by wildfire smoke).

  • I'd love to go back to NYC this year.

  • I'm also considering attending Laracon USA.

  • Do a founder's retreat with Jon (maybe in Chicago?).

  • More weekend trips with Lorinda!

  • I want to start a new podcast that I regularly publish every week. (Jeremy Enns and I are working on a short-run series on podcast growth right now).

  • I want to grow my newsletter, blog, podcast, and YouTube channel audience.

Justin Jackson

Connect with me on:
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Published on January 5th, 2024
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